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Stereoselective Synthesis of Vicinal Diamines
Author(s) -
Reetz Manfred T.,
Jaeger Ralf,
Drewlies Ralf,
Hübel Marcus
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199101031
Subject(s) - aldimine , vicinal , chemistry , chelation , stereoselectivity , nitrogen atom , cerium , reagent , deoxyribonucleoside , adduct , tosyl , medicinal chemistry , stereochemistry , organic chemistry , group (periodic table) , catalysis , enzyme
α‐Amino aldimines such as 1, which are readily accessible from amino acids , react with alkyllithium and ‐cerium compounds in a chelation‐controlled manner to give the vicinal diamines 2 in optical yields of up to 90%. However, if the donor strength of the aldimine nitrogen atom is weakened by the electron‐withdrawing tosyl group, the chelation effect is suppressed and reaction with Grignard reagents gives preferentially the stereoisomeric adducts with opposite relative configuration. Bn = benzyl.